Taber D F, Morrow J D, Roberts L J
Department of Chemistry and Biochemistry, University of Delaware, Newark 19716, USA.
Prostaglandins. 1997 Feb;53(2):63-7. doi: 10.1016/s0090-6980(97)00005-1.
In 1990, prostaglandin (PG) F2-like compounds were discovered to be produced in abundance in vivo by a free radical mechanism independent of the cyclooxygenase enzyme. Because these compounds are isomeric to cyclooxygenase-derived PGF2 alpha, they were termed F2-isoprostanes (F2-IsoP's). Subsequently, it was also demonstrated that PGD2-like compounds (D2-IsoP's) and PGE2-like compounds (E2-IsoP's) are also produced in vivo as products of this pathway. Four different regioisomers of each of these classes of IsoP's are formed, each of which can be comprised of eight racemic diastereomers. Thus, 64 different F2-IsoP's, E2-IsoP's, and D2-IsoP's can be formed. Interest in these molecules stems not only from the fact that quantification of IsoP's can provide a valuable index of free radical-induced lipid peroxidation in vivo but also from the fact that it has been shown that these compounds are capable of exerting potent biological activity. Because of this potential for exerting biological activity, the chemical syntheses of various IsoP compounds for biological testing has been initiated. As a result, a need for a systematic nomenclature for these compounds has evolved. A facile nomenclature that will allow rational differentiation and designation of each of the isomeric structures comprising the family of IsoP's is presented.
1990年，人们发现前列腺素（PG）F2样化合物在体内通过一种独立于环氧化酶的自由基机制大量产生。由于这些化合物与环氧化酶衍生的PGF2α是同分异构体，它们被称为F2异前列腺素（F2-IsoP's）。随后，还证明了PGD2样化合物（D2-IsoP's）和PGE2样化合物（E2-IsoP's）也作为该途径的产物在体内产生。这些类别的IsoP's中的每一种都形成四种不同的区域异构体，每种区域异构体都可以由八种外消旋非对映异构体组成。因此，可以形成64种不同的F2-IsoP's、E2-IsoP's和D2-IsoP's。对这些分子的兴趣不仅源于IsoP's的定量可以提供体内自由基诱导的脂质过氧化的有价值指标这一事实，还源于已证明这些化合物能够发挥强大的生物活性这一事实。由于这种发挥生物活性的潜力，已经开始进行各种IsoP化合物的化学合成以用于生物学测试。因此，对这些化合物的系统命名法的需求应运而生。本文提出了一种简便的命名法，该命名法将允许对构成IsoP's家族的每种异构体结构进行合理区分和指定。
